Cyanogen Bromide → HCID 13491944, compound

HRID 979782Notes

Reaction equation

HRID 979782 reaction equation
N#CBr.C[N:5]1[CH2:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C@@H:11]2[C@@H:6]1[CH2:7][C:8]1[C:9]3[C:22]([NH:23][CH:24]=1)=[CH:21][CH:20]=[CH:19][C:10]=32.C(=O)([O-])[O-].[K+].[K+]>C(Cl)(Cl)Cl>[CH:19]1[C:10]2[C@H:11]3[C@H:6]([CH2:7][C:8]4[C:9]=2[C:22]([NH:23][CH:24]=4)=[CH:21][CH:20]=1)[NH:5][CH2:18][C:17]1[C:12]3=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 10476Cyanogen BromideHCID 11430Potassium CarbonateHCID 10265374HCID 10265374, compound

Product 1

HCID 13491944HCID 13491944, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

38.6 g of cyanogen bromide are dissolved in 400 ml of chloroform. 20 g of trans-4,6,6a,7,8,12b-hexahydro-7-methylindolo[4,3-ab]phenanthridine are added to the solution whilst stirring, followed by 10 g of potassium carbonate. The resultant suspension is stirred overnight at room temperature, then filtered and the filtrate concentrated. The residue of evaporation is dissolved whilst heating in 400 ml of concentrated acetic acid, and then 55 ml of water, followed by 47.5 g of zinc powder, are added. The resultant suspension is stirred for 18 hours at 90°. The reaction solution is then filtered, the residue of filtration washed with methylene chloride/methanol, and the combined filtrates evaporated. The residue of evaporation is taken up in methylene chloride/methanol=9/1, and extracted with 1n aqueous sodium carbonate solution. The combined organic phases are washed with sodium chloride solution, dried over magnesium sulphate, filtered, concentrated and the residue chromatographed on silica gel, using methylene chloride/methanol=95/5 (CH2Cl2 10% saturated with NH3). The title compound is obtained. When crystallised from methanol, its hydrochloride melts at 301°-303°.

Workup

  1. filtrationfiltered
  2. concentrationthe filtrate concentrated
  3. customThe residue of evaporation
  4. dissolutionis dissolved
  5. temperaturewhilst heating in 400 ml of concentrated acetic acid
  6. additionare added
  7. stirringThe resultant suspension is stirred for 18 hours at 90°
  8. filtrationThe reaction solution is then filtered
  9. filtrationthe residue of filtration
  10. washwashed with methylene chloride/methanol
  11. customthe combined filtrates evaporated
  12. customThe residue of evaporation
  13. extractionextracted with 1n aqueous sodium carbonate solution
  14. washThe combined organic phases are washed with sodium chloride solution
  15. dry with materialdried over magnesium sulphate
  16. filtrationfiltered
  17. concentrationconcentrated
  18. customthe residue chromatographed on silica gel

Sources & evidence

ORD record
ord-abed7d025d264acf98d35a3e3aae3db5
Source dataset
uspto-grants-1987_01
Patent number
US04634708

Reaction notes

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